Application of a new nucleophilic addition/ring closure (NARC) sequence to the synthesis of enantiomerically-pure 2,8-dioxabicyclo[3.2.1]octanes of relevance to the squalestatins and zaragozic acids

被引:13
作者
Fallon, GD [1 ]
Jones, ED [1 ]
Perlmutter, P [1 ]
Selajarern, W [1 ]
机构
[1] Monash Univ, Dept Chem, Clayton, Vic 3168, Australia
关键词
D O I
10.1016/S0040-4039(99)01523-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
PL rapid method for the enantioselective construction of 2,8-dioxabicyclo[3.2.1]octanes of relevance to the zaragozic acids, employing a tandem NARC sequence of aldol and intramolecular Wacker reactions, is described. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7435 / 7438
页数:4
相关论文
共 35 条
  • [31] Enantioselective synthesis of a putative hexaketide intermediate in the biosynthesis of the squalestatins
    Simpson, TJ
    Smith, RW
    Westaway, SM
    Willis, CL
    Buss, AD
    Cannell, RJP
    Dawson, MJ
    Rudd, BAM
    [J]. TETRAHEDRON LETTERS, 1997, 38 (30) : 5367 - 5370
  • [32] Total synthesis of zaragozic acid A (squalestatin S1). Degradation to a relay compound and reassembly of the natural product
    Stoermer, D
    Caron, S
    Heathcock, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9115 - 9125
  • [33] Chiral dienolate chemistry in remote asymmetric induction: The allylation/Cope rearrangement sequence leading to gamma-chiral alpha,beta-unsaturated acid derivatives
    Tomooka, K
    Nagasawa, A
    Wei, SY
    Nakai, T
    [J]. TETRAHEDRON LETTERS, 1996, 37 (49) : 8895 - 8898
  • [34] Watson N S, 1996, Prog Med Chem, V33, P331, DOI 10.1016/S0079-6468(08)70308-4
  • [35] Chemoenzymatic studies: From cycloheptatriene to the core of zaragozic acids
    Xu, YP
    Johnson, CR
    [J]. TETRAHEDRON LETTERS, 1997, 38 (07) : 1117 - 1120